(+)-Styrene oxide → HCID 18607072, compound

HRID 1381268Notes

Reaction equation

HRID 1381268 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.[CH2:15]1[O:23][C@@H:16]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[OH:23][C@H:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][NH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH2:14])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 114705(+)-Styrene oxideHCID 144712494-(3-Aminopropyl)benzene-1-sulfonamide

Product 1

HCID 18607072HCID 18607072, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 20 g of 4-(3-aminopropyl)benzenesulphonamide, 16.8 g of (R)-styrene oxide and 500 ml of acetonitrile was heated under reflux for 40 hours. The solvent was then removed by evaporation in vacuo and the residue was chromatographed on 1 kg of silica gel. With chloroform/n-propanol25% ammonia (1600:100:4) there could be isolated 8.3 g of pure p-[3-[[(R)-β-hydroxyphenethyl]amino]propyl]benzenesulphonamide of melting point 165°-166° (from acetonitrile); [α]D20 =-13.4° (c=1.0% in methanol); ε224 =14710.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 hours
  3. customThe solvent was then removed by evaporation in vacuo
  4. customthe residue was chromatographed on 1 kg of silica gel

Sources & evidence

ORD record
ord-e0b45795a5264de39e056b39da8c9384
Source dataset
uspto-grants-1986_04
Patent number
US04585796

Reaction notes

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